Topical composition

ABSTRACT

The present invention relates to topical compositions comprising at least one liquid UV-filter and a nano-sized 1,4-di(benzoxazol-2′-yl)benzene.

The present invention relates to topical compositions comprising atleast one liquid UV-filter oil and a nano-sized1,4-di(benzoxazol-2′-yl)benzene as well as to the use of a nano-sized1,4-di(benzoxazol-2′-yl)benzene to reduce the transfer of UV-filter oilsto surfaces.

Sun care products have evolved considerably over the years. Earlierformulations were intended to protect the user from UV-B radiation aswas once thought that UV-B rays were the most important contributors towrinkling, skin disease, and skin cancer. However, more recent studieshave shown that UV-A radiation is equally or even more important in thedevelopment of solar damage and skin diseases, such as lupuserythematosus and melanoma and non-melanoma skin cancer. Thus, today'sfocus is towards eliminating as much of UVA (320-400 nm) and/or UVB(280-320 nm) light as possible. Consequently, there's a constantlyincreasing need for sun care products exhibiting high SPF's (SunProtection Factor) and at the same time high UVA protection while beingphotostable.

Accordingly, today's sun care products comprise significant amounts ofdifferent UV-filter substances such as in particular liquid UV-filtersoils to fulfill the above-mentioned requirements. Due to the resultinghigh oil load such sun care products however often exhibit unpleasantsensorial properties which knowingly reduce customer acceptability andthus lead to a reduction of the amounts applied to the skin, far belowthe recommended use level.

A further problem of such sun care products is that the materialcontained therein after application to a surface, particularly to theskin, is transferred to another surface when said surfaces are broughtinto contact with each other (also referred herein as ‘materialtransfer’). Such a transfer is nega¬tive in two ways: First of all, thetransfer of the material is not desired as it is re¬moved from the siteof action, such as treating, moisturizing or protecting the skin;Secondly, the surface of contact is contaminated with said material suchas in particular with oils which often results in staining of fabrics,such as clothes as well as in contamination of decorative or functionalsurfaces. The latter is not only negative in view of reducedfunctionality but also highly unwanted due to an unpleasant visualand/or aesthetic appearance. Particularly, displays of mobile phones,screens, spectacle glasses or touch screens are negatively affected bysuch material transfer as the material such as in particular the oilscontained therein renders the surfaces smeary which is highly unwantedby the end consumer. Accordingly, there exist a great desire to reducethe transfer of topical sun care products and in particular the oilscontained therein from surface to surface (in particular hard surfaces)when the surfaces are contacted.

Surprisingly, it has been found that compositions comprising at leastone liquid UV-filter oil in combination with a nano-sized1,4-di(benzoxazol-2′-yl)benzene exhibit a significantly reduced materialtransfer to a contacted surface such as particularly a glass surface.

Thus, the invention relates in one aspect to topical compositionscomprising at least one liquid UV-filter oil, wherein the compositionfurther comprises a nano-sized 1,4-di(benzoxazol-2′-yl)benzene.

The amount (total) of the at least one liquid UV-filter oil in thetopical compositions according to the present invention is preferablyselected in the range from 0.1 to 30 wt.-%, more preferably in the rangefrom 1 to 25 wt.-%, most preferably in the range from 5 to 20 wt.-%.

The amount of the nano-sized 1,4-di(benzoxazol-2′-yl)benzene (based onthe active) in the topical compositions according to the presentinvention is preferably selected in the range from 0.1 to 20 wt.-%, morepreferably in the range from 0.2 to 15 wt.-%, most preferably in therange from 0.3 to 10 wt.-%, based on the total weight of the topicalcomposition. Further suitable ranges are from 0.15 to 10 wt.-%, from 0.2to 10 wt.-% and from 0.5 to 10 wt.-%, based on the total weight of thetopical composition.

The term ‘topical’ as used herein is understood here to mean externalapplication to keratinous substances, which are in particular the skin,scalp, eyelashes, eyebrows, nails, mucous membranes and hair, preferablythe skin.

The term “material transfer” as used herein refers to the mass transferof the topical composition or some ingredients thereof when the topicalcomposition is applied to a surface and afterwards said surface isbrought in contact with a surface of a different object and separatedagain. By this contact some material is transferred from the firstsurface to the surface of the different object. The amount of materialtransferred can be determined by measuring the weight gain of the secondobject.

As the topical compositions according to the invention are intended fortopical application, it is well understood that they comprise aphysiologically acceptable medium, i.e. a medium compatible withkeratinous substances, such as the skin, mucous membranes, andkeratinous fibres. In particular the physiologically acceptable mediumis a cosmetically acceptable carrier.

The term ‘cosmetically acceptable carrier’ refers to all carriers and/orexcipients and/or diluents conventionally used in topical cosmeticcompositions such as in particular in sun care products.

Examples of such cosmetic carriers, excipients and diluents as well asadditives and active ingredients commonly used in the skin care industrywhich are suitable for use in the topical compositions of the presentinvention are for example described in the International CosmeticIngredient Dictionary & Handbook by Personal Care Product Council(http://www.personalcarecouncil.org/), accessible by the online INFOBASE (http://online.personalcarecouncil.org/jsp/Home.jsp), without beinglimited thereto.

The necessary amounts of the excipients, diluents, adjuvants, additivesetc. can, based on the desired product form and application, easily bedetermined by the skilled person. The additional ingredients can eitherbe added to the oily phase, the aqueous phase or separately as deemedappropriate.

In an advantageous embodiment, the topical compositions according to thepresent invention comprise from 50% to 99%, preferably from 60% to 98%,more preferably from 70% to 98%, such as in particular from 80% to 95%of a carrier, based on the total weight of the topical composition.

In a particular advantageous embodiment, the carrier consistsfurthermore of at least 40 wt. %, more preferably of at least 50 wt.-%,most preferably of at least 55 wt.-% of water, such as in particular of55 to 90 wt.-% of water.

The term ‘liquid UV-filter oil’ as used herein refers to any substancewhich absorbs light in the UVB and/or UVA range and which is liquid atambient temperature (i.e. 25° C.). Such UV-filter oils are well known toa person in the art and encompass in particular cinnamates such as e.g.octyl methoxycinnamate (PARSOL® MCX) and isoamyl methoxycinnamate (NeoHeliopan® E 1000), salicylates such as e.g. homosalate(3,3,5-trimethylcyclohexyl 2-hydroxybenzoate, PARSOL® HMS) andethylhexyl salicylate (also known as ethylhexyl salicylate, 2-ethylhexyl2-hydroxybenzoate, PARSOL® EHS), acrylates such as e.g. octocrylene(2-ethylhexyl 2-cyano-3,3-diphenylacrylate, PARSOL® 340) and ethyl2-cyano-3,3-diphenylacrylate, esters of benzalmalonic acid such as inparticular dialkyl benzalmalonates such as e.g. di-(2-ethylhexyl)4-methoxybenzalmalonate and polysilicone-15 (PARSOL® SLX), dialkylesterof naphthalates such as e.g. diethylhexyl 2,6-naphthalate (Corapan® TQ),syringylidene malonates such as e.g. diethylhexyl syringylidene malonate(Oxynex® ST liquid) as well as benzotriazolyl dodecyl p-cresol(Tinoguard® TL).

Particular advantageous liquid UV-filter oils in all embodiments of thepresent invention are octyl methoxycinnamate, homosalate, ethylhexylsalicylate, octocrylene, polysilicone-15, diethylhexyl 2,6-naphthalate,diethylhexyl syringylidene malonate and benzotriazolyl dodecyl p-cresolas well as mixtures thereof.

Most preferably in all embodiments of the present invention the liquidUV-filter oil is selected from the group consisting of octylmethoxycinnamate, homosalate, ethylhexyl salicylate, octocrylene,polysilicone-15 as well as mixtures thereof.

Particularly advantageous results are obtained with the liquidUV-filters octyl methoxycinnamate, homosalate and ethylhexyl salicylatewhich are accordingly most preferred.

The term nano-sized 1,4-di(benzoxazol-2′-yl)benzene refers to1,4-di(benzoxazol-2′-yl)benzene having a mean particle size in thenanometer range, i.e. of less than 1000 nm, preferably of less than 500nm, more preferably of less than 400 nm and most preferably of less than300 nm.

The term ‘mean particle size’ as used herein refers to the mean numberbased particle size distribution D_(n)50 (also known as D_(n)0.5) asdetermined by laser diffraction e.g. with a Malvern Mastersizer 2000(ISO 13320:2009).

In a particular advantageous embodiment, the nano-sized1,4-di(benzoxazol-2′-yl)benzene according to the present inventionexhibits a mean particle size D_(n)50 selected in the range from 10 to900 nm such as from 50 to 500 nm, more preferably from 50 to 400 nm,even more preferably from 100 to 300 nm, such as most preferably in therange from 120 to 280 nm, and even more preferably in the range from 140to 240 nm or in the range from 150 to 220 nm as determined by laserdiffraction (Malvern Mastersizer 2000).

Preferably, in all embodiments of the present invention, the nano-sized1,4-di(benzoxazol-2′-yl)benzene according to the present inventionfurthermore exhibits a D_(n)10 also known as D_(n)0.1) in the range from30 to 230 nm, more preferably in the range from 80 to 180 nm, mostpreferably in the range from 100 to 160 nm as determined by laserdiffraction (Malvern Mastersizer 2000).

Preferably, in all embodiments of the present invention, the nano-sized1,4-di(benzoxazol-2′-yl)benzene according to the present inventionfurthermore exhibits a D_(n)90 also known as D_(n)0.9) in the range from250 to 350 nm, more preferably in the range from 300 to 400 nm, mostpreferably in the range from 325 to 375 nm as determined by laserdiffraction (Malvern Mastersizer 2000).

Particular advantageous nano-sized 1,4-di(benzoxazol-2′-yl)benzeneaccording to the present invention exhibits a D_(n)10 in the range from100 to 160 nm, a D_(n)50 in the range from 150 to 220 nm and a D_(n)90in the range from 325 to 375 nm as determined by laser diffraction(Malvern Mastersizer 2000).

It is furthermore advantageous if the 1,4-di(benzoxazol-2′-yl)benzeneaccording to the present invention is a solid amorphous form of1,4-di(benzoxazol-2′-yl)benzene, as such solid amorphous formssurprisingly exhibits improved physical properties with regard toUV-absorption/protection, SPF contribution and formulation stabilitycompared to the respective crystalline forms.

The term “solid amorphous form,” as used herein, refers to solidparticles which are formed by fast formation/separation of a solid phasefrom a liquid phase in a solution or a mixture, so that the solid has notime to selectively form a crystal network and thus the obtained solidis in a predominantly disordered/semi-amorphous form (also referred toherein as ‘solid amorphous 1,4-di(benzoxazol-2′-yl)benzene’), which formcan be identified by XRPD analysis as illustrated herein. The solidamorphous 1,4-di(benzoxazol-2′-yl)benzene according to the presentinvention exhibits improved physical properties with regard toUV-absorption/protection, SPF contribution and formulation stabilitycompared to the respective crystalline form.

The solid amorphous form of micronized 1,4 di(benzoxazol-2′-yl)benzeneaccording to the present invention is characterized by a specificabsorbance E 1/1@320 nm of ≥750, preferably of ≥780, while therespective pure crystalline form exhibits a significantly lower specificabsorbance E 1/1, i.e. a E 1/1@320 nm of only 719 (based on the active).Thus, in a preferred embodiment, the solid amorphous form of 1,4di(benzoxazol-2′-yl)benzene according to the present invention ischaracterized by a specific absorbance E 1/1@320 nm of at least 750,more preferably of at least 780. Even more preferably the specificabsorbance E 1/1@320 nm is selected in the range from 780 to 850, mostpreferably in the range from 800 to 845.

The specific absorbance E1/1 (1 cm/1%) is well known to a person skilledin the art and is the (base line corrected) extinction corresponding toa concentration of a 1% (w/v) solution or dispersion of the testedcompound at an optical thickness of 1 cm at lambda max (i.e. thewavelength in the absorption spectrum where the absorbance is maximum).

The solid amorphous form of the micronized1,4-di(benzoxazol-2′-yl)benzene is furthermore characterized by an X-raypowder diffraction (XRPD) pattern substantially as depicted in FIG. 1,lines 3 and 4 which is substantially different to the one of crystalline1,4-di(benzoxazol-2′-yl)benzene (FIG. 1, lines 1 and 2). As can beretrieved from FIG. 1, the crystalline form is characterized by anunambiguous base line separation of the peaks at 25-28 °2Theta (CuK-alpha Radiation), while the solid amorphous form does not exhibit saidbase line separation. The X-ray diffraction patterns were recorded usinga Bruker D8 instrument with a LynxEye in reflection, using Cu Kαradiation.

In another (or even in an additional) embodiment, the solid amorphousform of 1,4-di(benzoxazol-2′-yl)benzene can also be characterized by itsdifferential scanning calorimetry (DSC) thermogram exhibiting an onsettemperature in the range of about 345 to 351 and a heat capacity in therange of about 115-135 J/g. DSC endotherms were recorded using a MettlerToledo DSC1 (Temperature range: 25° C. to 400° C.; heating rate: 4°C./min) as outlined in the examples.

The solid amorphous form of micronized 1,4-di(benzoxazol-2′-yl)benzeneaccording to the present invention is furthermore characterized by aratio of its UVB to UVA absorbance, which is ranging from 0.40 to 0.55,more preferably from 0.44 to 0.54, most preferably from 0.47 to 0.51.The ratio is determined by measuring the UV-spectra of the micronized1,4-di(benzoxazol-2′-yl)benzene dispersed in water at a concentration of0.001% (w/v) and calculating the ratio by dividing the area-% from 290to 319 nm (UVB) through the area-% from 320 to 400 nm (UVA).

The micronized 1,4-di(benzoxazol-2′-yl)benzene according to the presentinvention can be produced by standard micronization methods in the artas e.g. outlined in WO9522959, or WO9703643 which are included herein byreference.

The coarse particles of the 1,4-di(benzoxazol-2′-yl)benzene, i.e.particles having particle size of >350 nm can for example be prepared asoutlined in example 1 of WO2002039972 or as illustrated in the examplesof the present invention.

To obtain the micronized 1,4-di(benzoxazol-2′-yl)benzene according tothe present invention, coarse particles, more preferably coarseparticles of solid amorphous 1,4-di(benzoxazol-2′-yl)benzene, aremicronized by conventional grinding methods in the art until a particlesize with all the definitions and preferences as given herein isobtained, e.g. by grinding the coarse particles, preferably in thepresence of a grinding aid and optionally further customary additivesused in the preparation of micronized organic UV-filters, using knowngrinding apparatus, e.g. a jet, ball, vibration or hammer mill,preferably a high speed stirring mill. Preferably, modern ball mills areused; manufacturers of these types of mill are, for example, Netzsch(LMZ mill), Drais (DCP—Viscoflow or Cosmo), Bühler AG (centrifugalmills) or Bachhofer.

It is well understood, that the nano-sized1,4-di(benzoxazol-2′-yl)benzene according to the present invention isinsoluble in common cosmetic oils, wherein the term ‘insoluble’ refersto a solubility at RT (i.e. ˜22° C.) in common cosmetic oils such ase.g. C₁₂₋₁₅ alkyl benzoate, propyleneglycol, mineral oil but also inwater of less than 0.01 wt.-%, preferably of less than 0.05 wt.-%, mostpreferably of less than 0.03 wt.-% and thus remains in a particularstate after incorporation into a cosmetic or pharmaceutical compositionsuch as a sun care product.

The nano-sized 1,4-di(benzoxazol-2′-yl)benzene according to the presentinvention may be used in powder form or in the form of a dispersion ofthe nano-sized 1,4-di(benzoxazol-2′-yl)benzene. Preferably, in allembodiments of the present invention the nano-sized1,4-di(benzoxazol-2′-yl)benzene is used in the form of an aqueousdispersion of the nano-sized 1,4-di(benzoxazol-2′-yl)benzene as e.g.directly obtainable by wet milling processes.

The amount of the nano-sized 1,4-di(benzoxazol-2′-yl)benzene in suchaqueous dispersions is preferably selected in the range from 10 to 90wt.-%, 20 to 80 wt.-% or 30 to 70 wt-%, more preferably in the rangefrom 25 to 60 wt.-%, most preferably in the range from 25 to 55 wt.-%,based on the total weight of the aqueous dispersion.

It is well understood that such aqueous dispersions may containcustomary additives commonly used in the preparation of micronizedorganic UV-filters such as in particular grinding aids, wetting agents,thickeners, anti-foam agents and salts as well as mixtures thereof.

These additives can either be added before/during grinding or aftergrinding, e.g. to stabilize the aqueous dispersion.

The amount (total) of such additives in the aqueous dispersionsaccording to the present invention is preferably selected in the rangefrom 0.01 to 25 wt.-%, more preferably in the range from 2 to 20 wt.-%,most preferably in the range from 3 to 15 wt.-%, such as in the rangefrom 5 to 10 wt.-%, based on the total weight of the aqueous dispersion.

Suitable grinding aids are surface-active ingredients, that can be usedas dispersing agent such as in particular anionic, non-ionic, amphotericand cationic surfactants as well as mixtures thereof.

Most preferred in all embodiments according to the invention thegrinding aid is an alkyl poly-glucoside.

The term ‘alkyl poly-glucoside (APG)’ refers to a class of non-ionicsurfactants having the generic formula C_(n)H_(2+n)O(C₆H₁₀O₅)_(x)H, inwhich n is an integer selected in the range from 2 to 22 and x refers tothe mean polymerization level of the glucoside moiety (mono-, di-, tri-,oligo-, and poly-glucosides). These APG's are widely used in householdand industrial applications. They are generally derived from renewableraw materials such as glucose derived from corn and plant derived fattyalcohols. These alkyl poly-glucosides generally exhibit a meanpolymerisation level of the glucoside moiety ranging from 1 to 1.7,preferably from 1.2 to 1.6 such as from 1.4 to 1.6.

Particularly advantageous alkyl poly-glucosides are C₈₋₁₀ alkylpoly-glucosides consisting essentially of caprylyl (C₈) and capryl (C₁₀)poly-glucosides. Preferably such caprylyl (C₈) and capryl (C₁₀)poly-glucosides furthermore exhibit a ratio (%/%, wherein all % arearea-% determined by HPLC-MS) of caprylyl (C₈) mono-glucoside to capryl(C₁₀) mono-glucoside in the range from 3:1 to 1:3, preferably in therange from about 2:1 to 1:2, most preferably in the range from 1.5:1 to1:1.5. Additionally, such C₈₋₁₀ alkyl poly-glucoside preferably containno more than 3 wt.-%, more preferably no more than 2 wt.-%, mostpreferably no more than 1.5 wt.-% of C₁₂ alkyl mono-glucoside (asdetermined by HPLC-MS). It is understood, that such alkylpoly-glucosides are basically free of any higher (i.e. C₁₄₋₁₆) alkylpolyglucosides.

A particularly advantageous C₈₋₁₀ alkyl poly-glucoside in allembodiments of the present invention is made from glucose derived fromcorn and C₈ and C₁₀ fatty alcohols derived from coconut and palm kerneloils, which is e.g. sold as an aqueous dispersion under the tradenameGreen APG 0810 by Shanghai Fine Chemical.

The amount of the grinding aid in the aqueous dispersion according tothe present invention is preferably selected in the range from 1 to 20wt.-%, more preferably in the range from 2 to 15 wt.-%, most preferablyin the range from 5 to 10 wt.-%, based on the total weight of theaqueous dispersion.

Suitable antifoam agents encompass carrier oils, silicone oils andsilicone foam inhibitors, hydrophobic silica, hydrophobic fatderivatives and waxes, water-insoluble polymers, amphiphilic components,emulsifiers and coupling agents.

Particularly suitable anti-foam agents to be used in the aqueousdispersion according to the present invention are silicone oils such asin particular polydimethylsiloxanes and/or silicon anti-foam agents suchas in particular anhydrous dispersions of pyrogenic or hydrophobizedsilica in silicone oils such as most in particular simethicone. Mostpreferably in all embodiments of the present invention the anti-foamagent is simethicone.

The anti-foam agent(s) are preferably used in an amount (total) selectedin the range from 0 to 1 wt.-%, more preferably in an amount of 0.01 to0.2 wt.-%, based on the total weight of the aqueous dispersions.

Particularly suitable wetting agents to be used in the aqueousdispersion according to the present invention are(poly)propyleneglycol(s). Most preferably in all embodiments of thepresent invention the wetting agent is propyleneglycol.

Such wetting agent(s) are preferably used in an amount (total) selectedin the range from 0.1 to 1 wt.-%, more preferably in an amount of 0.2 to0.6 wt.-%, based on the total weight of the dispersion.

Particularly suitable thickeners to be used in the aqueous dispersionaccording to the present invention are xanthan gum, gellan gum and/orcarboxymethylcellulose. Most preferably in all embodiments of thepresent invention the thickener is xanthan gum or gellan gum.

Such thickener(s) are preferably used in an amount (total) selected inthe range from 0.1 to 1 wt.-%, more preferably in an amount of 0.1 to0.5 wt.-%, based on the total weight of the aqueous dispersion.

Suitable salts include alkali and earth alkaline salts of phosphate,hydroxide such as e.g. disodium hydrogen phosphate and/or sodiumhydroxide.

If present, the salt(s) are used in an amount (total) from 0.01 to 5wt.-%, preferably from 0.1 to 4 wt.-%, most preferably from 0.5 to 2.5wt.-%, based on the total weight of the aqueous dispersion.

The topical compositions of the present invention may be produced byphysically blending the nano-sized 1,4-di(benzoxazol-2′-yl)benzeneaccording to the present invention in powder form and a cosmeticallyacceptable carrier by any conventional method, e.g. by simply stirringthe two materials together.

In a preferred embodiment, however, the nano-sized1,4-di(benzoxazol-2′-yl)benzene is incorporated into the topicalcomposition in the form of an aqueous dispersion as outlined above,which is incorporated into the topical compositions according tostandard methods in the art.

Thus, in a preferred embodiment, the present invention relates totopical compositions comprising at least one liquid UV-filter oil and anaqueous dispersion of a nano-sized 1,4-di(benzoxazol-2′-yl)benzene withall the definitions and preferences as given herein.

In an even more preferred embodiment, said aqueous consists essentiallyof the micronized nano-sized 1,4-di(benzoxazol-2′-yl)benzene, preferablyin solid amorphous form, water and at least one additive selected fromthe group consisting of a grinding aid, a wetting agent, an anti-foamagent and a thickener as well as mixtures thereof.

Even more preferably the at least one further additive in said aqueousdispersion is a C₈₋₁₆ alkyl poly-glucoside and at least one furtheradditive selected from the group consisting of a propyleneglycol,xanthan gum, gellan gum and simethicone as well as mixtures thereof.

Most preferably in all embodiments according to the present inventionsaid aqueous dispersion consists essentially of

-   -   (i) 20-70 wt.-%, preferably 25-60 wt.-%, based on the total        weight of the aqueous dispersion, of the nano-sized        1,4-di(benzoxazol-2′-yl)benzene with all the preferences and        definitions as given herein,    -   (ii) 2 to 15 wt.-%, preferably 5 to 10 wt.-%, based on the total        weight of the aqueous dispersion, of a C₈₋₁₆ alkyl        poly-glucoside with all the preferences and definitions as given        above,    -   (iii) 0 to 3 wt.-%, preferably 0.1 to 2 wt.-%, based on the        total weight of the aqueous dispersion of at least one additive        selected from the group consisting of a wetting agent, an        anti-foam agent and a thickener as well as mixtures thereof, and    -   (iv) 25 to 60 wt.-%, preferably 30 to 45 wt.-%, based on the        total weight of the aqueous dispersion, of water.

The term ‘consisting essentially of’ as used according to the presentinvention means that the amounts of all ingredients such as theingredients (i) to (iv) sum up to 100 wt.-%. It is, however, notexcluded that small amount of impurities or additives may be presentwhich are, for example, introduced via the respective raw materials ofthe ingredients (i) to (iv).

Most preferably, the aqueous dispersion (I) contains as additives(iii-1) propyleneglycol, (iii-2) one thickener selected from xanthan gumor gellan gum and optionally (iii-3) simethicone.

As the micronized 1,4-di(benzoxazol-2′-yl)benzene according to thepresent invention significantly reduces the transfer of a topicalcomposition comprising at least one liquid UV-filter to surfaces, afurther aspect of the present invention is the use of the micronized1,4-di(benzoxazol-2′-yl)benzene as described and defined herein in atopical composition comprising at least liquid UV-filter for reducingthe material transfer to a contacted surface.

The amount of material transfer is determined by determination of theweight of the object (second object) before and after contact. Anyweight gain after contact is due to a material transfer from the firstto the second object. The reduction of material transfer is determinedby comparing compositions according to the inventions with therespective (not according to the invention) composition which does notcontain the micronized 1,4-di(benzoxazol-2′-yl)benzene according to thepresent invention. The reduction is expressed in % of the materialtransfer of the two measurements.

It has been found that the reduction of more than 20%, even more than25%, and even up to 45% can be obtained. Particular good results areobtained for O/W emulsions, which are accordingly particularlypreferred.

The topical composition is applied to a first surface. Said surface ispreferably skin, particularly human skin. It has been found that using aporous sponge instead of skin is a good approach for simulate a materialtransfer from skin to another surface.

The surface of the contacted object (second object) is preferably aglass surface or a plastic or a surface of a fabric.

In case the surface is a fabric, this is very advantages to avoid anunwanted transfer of topical composition to a fabric, particularly toclothes, as the cosmetic composition might stain the fabric.

Particularly, the contacted surface (i.e. surface of second object) is aglass surface.

Most preferably, the contacted surface (i.e. surface of second object)is an optical glass such as used for reading glasses or sunglasses or adisplay of screen of a smartphone display of a mobile phone, computerdevice or tablet.

By reducing the material transfer of the topical composition,particularly the problem of marks, particularly finger marks, left onglasses such as optical glasses of instruments or visual glasses whensaid glass surface is contacted with fingers can be reduced or evenavoided. Particularly, this can heavily reduce or even avoid anyundesired effects on the light rays transmitted through said glass bysaid material left on the surface.

Furthermore, marks left on the surface of an aesthetic surface such asof a mirror or a highly glossy or highly mat surface such as a of a topcoat of a car or furniture or piece of art, can be strongly reduced.This is very advantageous as such surfaces need a high amount ofcleaning maintenance, if they are brought in contact with skin on whichtopical compositions have been applied, particularly if they are touchedby fingers which have been previously in contact with topicalcompositions.

Marks left on the surface of display units, such as displays of mobilephones, screens, or touch screens of monitors, laptops, mobile phones ortablets can be strongly reduced. As a result of this, the readabilitycan be improved. As the functionality of touch screens depends onsurface aspects, the invention helps also to improve constant touchscreen functionality without excessive need of cleaning said glasssurface.

The reduction of material transfer also heavily reduces the labour andcost involved in the cleaning of said surfaces when they are contactedwith skin.

As the nano-sized 1,4-di(benzoxazol-2′-yl)benzene significantly reducesthe transfer of a topical composition to surfaces, the present inventionfurther relates to

-   -   a method for the use of the nano-sized        1,4-di(benzoxazol-2′-yl)benzene as described and defined herein        in a topical composition comprising at least one UV-filter oil        for reducing the transfer of the topical composition to glass or        plastic surfaces.    -   a method for the use of nano-sized        1,4-di(benzoxazol-2′-yl)benzene according to the present        invention in a topical composition comprising at least one        liquid UV-filter oil for reducing the transfer of the topical        composition to glass or plastic surfaces.    -   a use of a nano-sized 1,4-di(benzoxazol-2′-yl)benzene as        described and defined herein to reduce the transfer of a topical        composition comprising at least one UV-filter oil to a surface        such as in particular to a glass or plastic surface.    -   a method to reduce the transfer of a topical composition        comprising at least one liquid UV-filter oils to a surface such        as in particular to a glass or plastic surface, said method        encompassing the addition of a nano-sized        1,4-di(benzoxazol-2′-yl)benzene as described and defined herein        to a topical composition comprising at least one liquid        UV-filter oil.

In a further embodiment, the present invention relates to the topicalcomposition according to the embodiments described herein for the use assunscreen, respectively to the use of the topical composition accordingto the embodiments described herein as sunscreen.

Preferred topical compositions according to the invention are skin carepreparations, decorative preparations, and functional preparations.

Examples of skin care preparations are, in particular, light protectivepreparations, anti-ageing preparations, preparations for the treatmentof photo-ageing, body oils, body lotions, body gels, treatment creams,skin protection ointments, skin powders, moisturizing gels, moisturizingsprays, face and/or body moisturizers, skin-tanning preparations (i.e.compositions for the artificial/sunless tanning and/or browning of humanskin), for example self-tanning creams as well as skin lighteningpreparations.

Examples of decorative preparations are, in particular, lipsticks, eyeshadows, mascaras, dry and moist make-up formulations, rouges and/orpowders.

Examples of functional preparations are cosmetic or pharmaceuticalcompositions containing active ingredients such as hormone preparations,vitamin preparations, vegetable extract preparations, anti-ageingpreparations, and/or antimicrobial (antibacterial or antifungal)preparations without being limited thereto.

In a particular embodiment, the topical compositions according to theinvention are light-protective preparations (sun care products), such assun protection milks, sun protection lotions, sun protection creams, sunprotection oils, sun blocks or day care creams with a SPF (sunprotection factor). Of particular interest are sun protection creams,sun protection lotions, sun protection milks and sun protectionpreparations.

The topical compositions according to the present invention may be inthe form of a suspension or dispersion in solvents or fatty substances,or alternatively in the form of an emulsion or micro emulsion (inparticular of oil-in-water (O/W-) or water-in-oil (W/O-)type,silicone-in-water (Si/W-) or water-in-silicone (W/Si-)type,PIT-emulsion, multiple emulsion (e.g. oil-in-water-in oil (O/W/O-) orwater-in-oil-in-water (W/O/W-)type), pickering emulsion, hydrogel,alcoholic gel, lipogel, one- or multiphase solution or vesiculardispersion or other usual forms, which can also be applied by pens, asmasks or as sprays.

Preferred topical compositions in all embodiments of the presentinvention are emulsions which contain an oily phase and an aqueous phasesuch as in particular O/W, W/O, Si/W, W/Si, O/W/O, W/O/W multiple or apickering emulsions.

The amount of the oily phase (i.e. the phase containing all oils andfats including the UV-filter oils) present in such emulsions ispreferably at least 10 wt.-%, such as in the range from 10 to 60 wt.-%,preferably in the range from 15 to 50 wt.-%, most preferably in therange from 15 to 40 wt.-%, based on the total weight of the topicalcomposition.

The amount of the aqueous phase present in such emulsions is preferablyat least 20 wt.-%, such as in the range from 20 to 90 wt.-%, preferablyin the range from 30 to 80 wt.-%, most preferably in the range from 30to 70 wt.-%, based on the total weight of the topical composition.

More preferably, the topical compositions according to the presentinvention are in the form of an oil-in-water (O/W) emulsion comprisingan oily phase dispersed in an aqueous phase in the presence of an O/W-respectively Si/W-emulsifier. The preparation of such O/W emulsions iswell known to a person skilled in the art and illustrated in theexamples.

In an advantageous embodiment, the O/W emulsifier is a phosphate esteremulsifier. A particular phosphate ester emulsifier according to theinvention is potassium cetyl phosphate e.g. commercially available asAmphisol® K at DSM Nutritional Products Ltd Kaiseraugst.

A particularly suitable W/O- or W/Si-emulsifiers ispolyglyceryl-2-dipolyhydroxystearate.

The at least one W/O emulsifier is preferably used in an amount of about0.001 to 10 wt.-%, more preferably in an amount of 0.2 to 7 wt.-% withrespect to the total weigh of the composition.

The topical compositions according to the present invention furthermoreadvantageously contain at least one co-surfactant such as e.g. selectedfrom the group of mono- and diglycerides and/or fatty alcohols. Theco-surfactant is generally used in an amount selected in the range from0.1 to 10 wt.-%, such as in particular in the range from 0.5 to 6 wt.-%,such as most in particular in the range from 1 to 5 wt.-%, based on thetotal weight of the composition. Particular suitable co-surfactants areselected from the list of alkyl alcohols such as cetyl alcohol (LorolC16, Lanette 16), cetearyl alcohol (Lanette O), stearyl alcohol (Lanette18), behenyl alcohol (Lanette 22), glyceryl stearate, glyceryl myristate(Estol 3650), hydrogenated coco-glycerides (Lipocire Na10) as well asmixtures thereof

The compositions in form of O/W emulsions according to the invention canbe provided, for example, in all the formulation forms for O/Wemulsions, for example in the form of serum, milk or cream, and they areprepared according to the usual methods. The compositions which aresubject-matters of the invention are intended for topical applicationand can in particular constitute a dermatological or cosmeticcomposition, for example intended for protecting human skin against theadverse effects of UV radiation (antiwrinkle, anti-ageing, moisturizing,anti-sun protection and the like).

According to an advantageous embodiment of the invention thecompositions constitute cosmetic composition and are intended fortopical application to the skin.

Finally, a subject-matter of the invention is a method for the cosmetictreatment of keratinous substances such as in particular the skin,wherein a topical composition as defined herein is applied to the saidkeratinous substances such as in particular to the skin. The method isin particular suitable to protect the skin against the adverse effectsof UV-radiation such as in particular sun-burn and/or photoageing.

In accordance with the present invention, the compositions according tothe invention may comprise further ingredients such as ingredients forskin lightening; tanning prevention; treatment of hyperpigmentation;preventing or reducing acne, wrinkles, lines, atrophy and/orinflammation; chelators and/or sequestrants; anti-cellulites andslimming (e.g. phytanic acid), firming, moisturizing and energizing,self-tanning, soothing, as well as agents to improve elasticity and skinbarrier and/or further UV-filter substances and carriers and/orexcipients or diluents conventionally used in topical compositions. Ifnothing else is stated, the excipients, additives, diluents, etc.mentioned in the following are suitable for topical compositionsaccording to the present invention. The necessary amounts of thecosmetic and dermatological adjuvants and additives can, based on thedesired product, easily be determined by the skilled person. Theadditional ingredients can either be added to the oily phase, theaqueous phase or separately as deemed appropriate. The mode of additioncan easily be adapted by a person skilled in the art.

The cosmetically active ingredients useful herein can in some instancesprovide more than one benefit or operate via more than one mode ofaction.

The topical cosmetic compositions of the invention can also containusual cosmetic adjuvants and additives, such aspreservatives/antioxidants, fatty substances/oils, water, organicsolvents, silicones, thickeners, softeners, emulsifiers, sunscreens,antifoaming agents, moisturizers, aesthetic components such asfragrances, surfactants, fillers, sequestering agents, anionic,cationic, nonionic or amphoteric polymers or mixtures thereof,propellants, acidifying or basifying agents, dyes, colorings/colorants,abrasives, absorbents, essential oils, skin sensates, astringents,antifoaming agents, pigments or nanopigments, e.g. those suited forproviding a photoprotective effect by physically blocking outultraviolet radiation, or any other ingredients usually formulated intocosmetic compositions.

Such cosmetic ingredients commonly used in the skin care industry, whichare suitable for use in the compositions of the present invention arefor example described in the International Cosmetic IngredientDictionary & Handbook by Personal Care Product Council(http://www.personalcarecouncil.org/), accessible by the online INFOBASE (http://online.personalcarecouncil.org/jsp/Home.jsp), without beinglimited thereto.

The necessary amounts of the cosmetic and dermatological adjuvants andadditives can—based on the desired product—easily be chosen by a skilledperson in this field and will be illustrated in the examples, withoutbeing limited hereto.

Of course, one skilled in this art will take care to select the abovementioned optional additional compound or compounds and/or their amountssuch that the advantageous properties intrinsically associated with thecombination in accordance with the invention are not, or notsubstantially, detrimentally affected by the envisaged addition oradditions.

The topical compositions according to the invention in general have a pHin the range from 3 to 10, preferably a pH in the range from 4 to 8 andmost preferably a pH in the range from 4 to 7. The pH can easily beadjusted as desired with suitable acids such as e.g. citric acid orbases such as NaOH according to standard methods in the art.

The topical compositions according to the invention may further containone or more emollients which soothe and soften the skin. As an example,the emollient may be dicaprylyl carbonate. Further emollients aresilicone (dimethicone, cyclomethicone), vegetable oils (grape seed,sesame seed, jojoba, etc.), butters (cocoa butter, shea butter),alcohols, and petrolatum derivatives (petroleum jelly, mineral oil).

The cosmetic compositions according to the present inventionadvantageously comprise preservatives or preservative booster. Whenpresent, the preservative respectively preservative booster ispreferably used in an amount of 0.01 to 2 wt.-%, more preferably in anamount of 0.05 to 1.5 wt.-%, most preferably in an amount of 0.1 to 1.0wt.-%, based on the total weight of the composition. It is particularlypreferred, that the cosmetic compositions according to the inventiondoes not contain any preservatives selected from the group of parabensand/or methylisothiazolidine.

The following examples are provided to further illustrate thecompositions and effects of the present invention. These examples areillustrative only and are not intended to limit the scope of theinvention in any way.

EXAMPLES 1. Preparation of Nano-Sized 1,4-di(benzoxazol-2′-yl)benzene

1.1 General Methods:

All particles sizes have been determined by laser diffraction with aMalvern Mastersizer 2000 according to the method as outlined in ISO13320:2009 and/or a Coulter Delsa Nano S (dynamic laser scattering).

Differential scanning calorimetry (DSC) was performed using MettlerToledo DSC1 (temperature range from 25° C. to 400° C.; heating rate: 4°C./min; air atmosphere, 2-3 mg samples, average from 2 measurements).

X-ray diffraction patterns were recorded using a Bruker D8 Advancepowder X-ray diffractometer in reflection (Bragg-Brentano) geometry. ThePXRD diffractometer was equipped with a LynxEye detector. The sampleswere generally prepared without any special treatment other than theapplication of slight pressure to get a flat surface. Silicon singlecrystal sample holder for polymorph screening, 1.0 mm depth. Sampleswere measured uncovered. The tube voltage was 40 kV and current was 40mA. A variable divergence slight was used with a 3° window. The stepsize was 0.02 °2θ with a step time of 37 seconds. The samples wererotated at 0.5 rps during the measurement.

E 1/1 values were determined with a UV/(vis) spectrometer (Perkin ElmerLambda 650S) at 320 nm and a baseline correction according to thefollowing formula: E 1/1=(E 1/1@320 nm)−(E 1/1@650 nm).

The UVB:UVA ratio was determined by measuring the UV-spectra of therespective micronized UV-filter dispersed in water at a concentration of0.001% (w/v) active and calculating the ratio by dividing the area-%from 290 to 319 nm (UVB) through the area-% from 320 to 400 nm (UVA).

1.2 Preparation of Coarse Particles of Solid Amorphous1,4-di(benzoxazol-2′-yl)benzene (DBO-400 (A))

A mixture of 702 g polyphosphoric acid and 4.28 ml methanesulfonic acidwas heated to 90° C. 65 g terephthalic acid and 107 g 2-aminophenol wereadded. The mixture was stirred under inert atmosphere at 180° C. for 8hours and then transferred to ice water. The precipitated product wasfiltered and washed with water and acetic acid. The precipitate wasdispersed in water and the pH adjusted to 8.0 with sodium hydroxide,filtered and washed with water. The crude product was suspended in amixture of toluene and 1-butanol 3.3:1, stirred at 85° C. for one hour,filtered, washed with diethyl ether, and dried. The resulting coarseparticles of solid amorphous 1,4-di(benzoxazol-2′-yl)benzene exhibited aparticle size Dn50 of 380 nm (Malvern).

1.3 Preparation of an Aqueous Dispersion of Solid Amorphous1,4-di(benzoxazol-2′-yl)benzene (DBO-200 Dispersion (A))

A suspension of 175 g of DBO-400 obtained as outlined in (1), 324 g ofwater and 65 g Green APG 0810 was prepared. Afterwards the suspensionwas milled for 2 h with a LabStar laboratory mill usingyttrium-stabilized zirconium oxide grinding beads (0.3 mm, from TosohCeramic, Japan) and cooling of the milling chamber (−12° C. brine).After removal of the grinding beads, a 30% aqueous dispersion ofmicronized 1,4-di(benzoxazol-2′-yl)benzene was obtained.

Particle Size:

-   -   Malvern: Dn50 186 nm (Dn10=126 nm, Dn90=355 nm)    -   Coulter: Mean value (intensity distribution): 171 nm

E 1/1: 839

DSC: onset temperature: 350° C.; heat capacity: 132 J/g.

Ratio UVB:UVA: 0.49

X-ray: FIG. 1, line 4

1.4 Preparation of an Aqueous Dispersion of Crystalline1,4-di(benzoxazol-2′-yl)benzene (DBO-200 Dispersion (C))

After recrystallisation of coarse particles obtained as outlined in(1.2) from o-dichlorobenzene and drying 73.0% of crystalline1,4-di(benzoxazol-2′-yl)benzene was obtained, which was subsequentlymilled in analogy to the process outlined in (1.3). After removal of thegrinding beads a 30% aqueous dispersion of crystalline1,4-di(benzoxazol-2′-yl)benzene was obtained.

Particle Size:

-   -   Coulter: Mean value (intensity distribution): 193 nm

E 1/1: 719;

DSC: Onset temperature: 352° C.; heat capacity: 153 J/g.

Ratio UVB:UVA: 0.35

X-ray: FIG. 1, line 2

1.5 Preparation of an Aqueous Dispersion of Coarse Solid Amorphous1,4-di(benzoxazol-2′-yl)benzene (DBO-400 Dispersion (A))

A suspension of 1.8 g of DBO-400 obtained as outlined in (1), 3.51 g ofwater and 0.69 g of Green APG 0810 was prepared. Afterwards thesuspension was mixed at ambient temperature (22° C.) with a magneticmixture until a homogenous dispersion was obtained. After removal of themagnetic stir bar a 30% aqueous dispersion of micronized1,4-di(benzoxazol-2′-yl)benzene having a mean particle size Dn50 of 380nm (Malvern) was obtained.

2. Material Transfer

The material transfer has been determined with the sponge test asoutlined in the following:

-   -   Cut a sponge cloth (Weitawip Claire, from Weita AG:        cellulose/cotton fiber mixture, 200 g/m², 5 mm thickness) into        pieces of 76 mm×26 mm    -   Tare the sponge sample    -   Apply 400 mg of the respective sample(=cosmetic composition) and        distribute homogenously all over the sponge surface of 76 mm×26        mm    -   Weigh the sponge with the applied sample    -   Tare a microscope slide (glass plate 76 mm×26 mm×1 mm)    -   Put the microscope slide (glass plate) on top of the sponge, on        which a balance weight of 500 g (height: 6.3 cm, diameter at        area of contact: 3.7 cm) is placed for 10 seconds to apply a        specific pressure to the sample    -   Remove cautiously vertically the microscope slide    -   Weigh the removed microscope slide and determine accordingly the        amount of sample transferred to the glass plate    -   Repeat the test for each composition 10 times to receive an        average value (mean value) for each sample.

2.1 Material Transfer in Dependence of the Particle Size

The formulations as outlined in table 1 have been prepared according tostandard methods in the art. Afterward the material transfer wasassessed as outlined above.

TABLE 1 Results of the material transfer (I) INCI Ref-1 Inv-1 Inv-2Wt.-% Potassium Cetyl Phosphate 1.50 1.50 1.50 Cetyl alcohol 3.00 3.003.00 Cetearyl alcohol 1.00 1.00 1.00 Caprylic/Capric triglyceride 8.008.00 8.00 Aqua Ad 100 Ad 100 Ad 100 Glycerin 3.00 3.00 3.00 Xanthan Gum0.30 0.30 0.30 Preservative 1.00 1.00 1.00 Octocrylene 8.00 8.00 8.00DBO 400 nm, Aqua, Decyl Glucoside — 2.4* — (30% active) (DBO-400dispersion (A)) DBO 200 nm, Aqua, Decyl Glucoside — — 2.4* (30% active)(DBO-200 dispersion (A)) Transfer of cream 1.7% 1.3% 0.8% *Based onactive

As can be retrieved from table 1, the addition of the nano-sized organicUV-filter according to the present invention significantly reduced theamount of cream transferred to the glass surface compared to thereference rendering the glass surfaces less smeary compared to thereferences.

2.2 Material Transfer in Dependence of the Particle Size and the LiquidUV-Filter Oil

The formulations as outlined in table 2 have been prepared according tostandard methods in the art. Afterward the material transfer wasassessed as outlined above.

TABLE 2 Results of the material transfer (II) INCI Inv-3 Inv-4 Inv-5Inv-6 Inv-7 Inv-8 Inv-9 Inv-10 Wt.-% Potassium Cetyl Phosphate 1.5 1.51.5 1.5 1.5 1.5 1.5 1.5 Cetyl alcohol 3.0 3.0 3.0 3.0 3.0 3.0 3.0 3.0Cetearyl alcohol 1.0 1.0 1.0 1.0 1.00 1.0 1.00 1.0 Caprylic/Caprictriglyceride 8.0 8.0 8.0 8.0 8.0 8.0 8.0 8.0 Aqua Ad 100 Glycerin 3.03.0 3.0 3.00 3.0 3.0 3.0 3.0 Xanthan Gum 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3Preservative 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Homosalate 10.0 10.0Ethylhexyl salicylate 5.0 5.0 Polysilicone-15 3.0 3.0 Octylmethoxycinnamate 5.0 5.0 DBO-200 dispersion (A) 2.4* — 2.4* — 2.4* —2.4* — DBO-400 (A) — 2.4* — 2.4* — 2.4* — 2.4* % Transfer 0.49 3.11 0.402.73 0.78 3.76 0.66 2.59 *Based on active

As can be retrieved from table 2, the addition of the nano-sized1,4-di(benzoxazol-2′-yl)benzene having a particle size of less than 300nm exhibited an even more pronounced reduction of the amount of the oilstransferred to the glass surface compared to the particles having aparticle size of >300 nm rendering the glass surfaces even less smeary.Furthermore, the use of the UV-filter oils octylmethoxycinnamate,ethylhexylsalicylate and homosalate resulted in the best results.

2.3 Material Transfer in Dependence of Emulsion Type

The formulations as outlined in table 3 have been prepared according tostandard methods in the art. Afterward the material transfer wasassessed as outlined above.

TABLE 3 Results of the material transfer (III) Inv-11 Inv-12 Inv-13Inv-14 INCI O/W W/O O/W W/O Wt.-% Potassium Cetyl 1.5 PhosphatePolyglyceryl-2- 5.0 5.0 5.0 dipolyhydroxystearate Cetyl alcohol 3.0Cetearyl alcohol 1.0 Microcristalline wax 2.0 2.0 2.0 Caprylic/Capric 1515 15 triglyceride Ethylhexyl 5.0 5.0 salicylate Octocrylene 8.0 8.0Aqua Ad 100 Glycerin 3.0 3.0 3.0 3.0 Xanthan Gum 0.3 Magnesium sulfate1.0 1.0 1.0 heptahydrate preservative 1.0 0.5 0.5 0.5 DBO-200 dispersion2.4* 2.4* 2.4*− 2.4* (A) Transfer [%] 0.4 1.26 0.8 1.73 *Based on active

As can be retrieved from the table, the addition of the nano-sized1,4-di(benzoxazol-2′-yl)benzene according to the present inventionsignificantly reduced the amount of the cream transferred to the glasssurface compared to the references rendering the glass surfaces lesssmeary compared to the references. Additionally, the transfer issignificantly lower in the O/W formulations than in the respective W/Oformulations.

3. UV-Performance of the Solid Amorphous Versus Crystalline Form

The formulations as outlined in table 4 have been prepared according tostandard methods in the art. Afterward the in vitro SPF was assesseddirectly after manufacturing (t0) and after 1-month storage at RT (t1).The in vitro SPF test was performed on PMMA plates (WW5 from Schönberg,5 cm×5 cm, roughness of 5 μm): 32.5 mg of the respective formulation(i.e. 1.3 mg/cm²) were applied homogenously onto the PMMA plates anddried for 15 minutes.

The in vitro SPF was determined using a Labsphere 2000 UV TransmittanceAnalyzer: each PMMA plate was measured 9 times at different points onthe plate resulting in 27 data points. The result is calculated as theaverage of these 27 data points.

TABLE 4 in vitro SPF Ingredient Wt.-% Wt.-% Potassium Cetyl Phosphate1.8 1.8 Glyceryl Stearate 2.0 2.0 Stearyl Alcohol 2.5 2.5 IsopropylMyristate 2.0 2.0 C12-15 Alkyl Benzoate 5.0 5.0 Caprylic/CapricTriglyceride 5.0 5.0 Xanthan Gum 0.4 0.4 Aqua Ad 100 Ad 100 Preservative1.0 1.0 amorphous DBO (30% active) 3*  (DBO-200 dispersion (A))crystalline DBO (30% active) 3*  (DBO-200 dispersion (C)) In vitro SPF @t0 9.1 6.5 In vitro SPF @ t1 8.7 2.9 Critical wavelength 379    382   *based on the active (i.e. 10 wt.-% of the respective dispersion)

As can be retrieved from table 4 the use of solid amorphous DBO resultsin a significantly higher SPF compared to the respective crystallineform. Furthermore, such formulations are more storage stable asreflected by an unchanged in vitro SPF after 1-month storage @ RT forthe solid amorphous form compared to a significantly reduced SPF after1-month storage @ RT for of the respective crystalline form.

1. A topical composition comprising a substance which absorbs light inthe UVB and/or UVA range and which is liquid at ambient temperature(UV-filter oil), wherein the composition further comprises a nano-sized1,4-di(benzoxazol-2′-yl)benzene having a mean particle size D_(n)50determined by laser diffraction of less than 1000 nm, preferably of lessthan 500 nm, most preferably of less than 400 nm.
 2. The topicalcomposition according to claim 1, wherein the amount of the at least oneUV-filter oil is selected in the range from 0.1 to 30 wt.-%, morepreferably in the range from 1 to 25 wt.-%, most preferably in the rangefrom 5 to 20 wt.-%.
 3. The topical composition according to claim 1,wherein the amount of the nano-sized 1,4-di(benzoxazol-2′-yl)benzene isselected in the range from 0.1 to 20 wt.-%, preferably in the range from0.2 to 15 wt.-%, most preferably in the range from 0.3 to 10 wt.-%,based on the total weight of the topical composition.
 4. The topicalcomposition according to claim 1, wherein the at least one UV-filter oilis selected from the group consisting of octyl methoxycinnamate,homosalate, ethylhexyl salicylate, octocrylene, polysilicone-15,diethylhexyl 2,6-naphthalate, diethylhexyl syringylidene malonate andbenzotriazolyl dodecyl p-cresol as well as mixtures thereof, preferablyof octyl methoxycinnamate, homosalate and/or ethylhexyl salicylate. 5.The topical composition according to claim 1, wherein the nano-sized1,4-di(benzoxazol-2′-yl)benzene has a mean particle size D_(n)50determined by laser diffraction selected in the range from 50 to 300 nm,more preferably in the range from 120 to 280 nm, most preferably in therange from 150 to 220 nm.
 6. The topical composition according to claim1, wherein the nano-sized 1,4-di(benzoxazol-2′-yl)benzene is1,4-di(benzoxazol-2′-yl)benzene in a solid amorphous form.
 7. Thetopical composition according to claim 1, wherein the nano-sized1,4-di(benzoxazol-2′-yl)benzene is incorporated into the topicalcomposition in the form of an aqueous dispersion containing nano-sizedparticles of 1,4-di(benzoxazol-2′-yl)benzene.
 8. The topical compositionaccording to claim 1, wherein the topical composition is an emulsioncontaining an oily phase and an aqueous phase.
 9. The topicalcomposition according to claim 1, wherein the amount of the oily phaseis at least 10 wt.-%, based on the total weight of the topicalcomposition.
 10. The topical composition according to claim 1, whereinthe amount of the oily phase is selected in the range from 10 to 60wt.-%, preferably in the range from 15 to 50 wt.-%, most preferably inthe range from 15 to 40 wt.-%, based on the total weight of the topicalcomposition.
 11. The topical composition according to claim 1, whereinthe topical composition is in the form of an oil-in-water (O/W) emulsioncomprising an oily phase dispersed in an aqueous phase in the presenceof an O/W emulsifier.
 12. The topical composition according to claim 11,wherein the O/W emulsifier is a phosphate ester emulsifier.
 13. Thetopical composition according to claim 12, wherein the phosphate esteremulsifier is a cetyl phosphate.
 14. Use of a nano-sized1,4-di(benzoxazol-2′-yl)benzene having a mean particle size D_(n)50determined by laser diffraction of less than 1000 nm, preferably of lessthan 500 nm, most preferably of less than 400 nm to reduce the transferUV-filter oil(s) contained in a topical composition to a surface. 15.Method to reduce the transfer of liquid UV-filter oil(s) to a surfacesuch as in particular to a glass or plastic surface, said methodencompassing the addition of a nano-sized1,4-di(benzoxazol-2′-yl)benzene having a mean particle size D_(n)50determined by laser diffraction of less than 1000 nm, preferably of lessthan 500 nm, most preferably of less than 400 nm into a topicalcomposition comprising such liquid UV-filter oil(s).